Lower Sugarloaf Key Holiday Rentals

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Our top choices for Lower Sugarloaf Key holiday rentals

Old Wooden Bridge Resort and Marina

2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (276)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
Old Town Key West
8.4 out of 10, Very good, (319)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is HK$2,069
HK$2,590 total
includes taxes & fees
15 Dec - 16 Dec
Hyatt Vacation Club at Sunset Harbor, Key West

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is HK$1,022
HK$2,454 total
includes taxes & fees
10 Dec - 11 Dec
Aqua Lodges at Hurricane Hole Marina

Steps from Duval, Pool on Site & Bikes Included!

Old Town Key West
9.6 out of 10, Exceptional, (411)
"Everything was excellent!"
United States
Susan L.
The price is HK$693
HK$1,770 total
includes taxes & fees
10 Dec - 11 Dec
Steps from Duval, Pool on Site & Bikes Included!

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Old Town Key West
10.0 out of 10, Exceptional, (26)
"Will stay here again "
United States
Matt O.
The price is HK$1,152
HK$3,151 total
includes taxes & fees
15 Dec - 16 Dec
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is HK$1,945
HK$3,898 total
includes taxes & fees
10 Dec - 11 Dec
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Old Town Key West
10.0 out of 10, Exceptional, (24)
"We had a wonderful stay here with our kids. Can’t beat the location."
United States
Julia P.
The price is HK$1,152
HK$3,151 total
includes taxes & fees
17 Dec - 18 Dec
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Heated Pool, Steps to Duval St - Poolside Paradise

Old Town Key West
9.2 out of 10, Wonderful, (18)
"Great location"
United States
Peter S.
The price is HK$5,477
HK$10,643 total
includes taxes & fees
16 Dec - 17 Dec
Heated Pool, Steps to Duval St - Poolside Paradise

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
Key West
8.2 out of 10, Very good, (821)
"The staff goes above and beyond very, very warm and nice people"
United States
erik
Coconut Mallory Resort And Marina By Kees Vacations

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Sands
The price is HK$1,471
HK$4,420 total
includes taxes & fees
15 Dec - 16 Dec
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Private Parking, Heated Pool - Sweet Caroline

Key West Historic District
8.6 out of 10, Excellent, (20)
"It is definitely an historic property with some cracks in the floor boards and bathrooms but it has its charms and the location is excellent! I would stay there again!"
United States
Martha B.
Private Parking, Heated Pool - Sweet Caroline

Spacious home with pool & balcony - 1 block from Duval Street

Key West Historic District
9.2 out of 10, Wonderful, (84)
"Great location! Close to all the activities."
United States
susan h.
The price is HK$4,668
HK$8,301 total
includes taxes & fees
15 Dec - 16 Dec
Spacious home with pool & balcony - 1 block from Duval Street

Private Heated Pool & Near Duval - The Curry House

Old Town Key West
10.0 out of 10, Exceptional, (6)
"Great property! "
United States
Austin C.
The price is HK$17,910
HK$34,527 total
includes taxes & fees
6 Jan - 7 Jan 2026
Private Heated Pool & Near Duval - The Curry House

Island View 1BR Residence With Balcony

2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is HK$1,767
HK$2,650 total
includes taxes & fees
23 Dec - 24 Dec
Island View 1BR Residence With Balcony

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Old Town Key West
10.0 out of 10, Exceptional, (195)
"Outstanding place to stay, centrally located!"
United States
Elizabeth Y.
The price is HK$9,336
HK$17,203 total
includes taxes & fees
15 Dec - 16 Dec
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Luxury Waterfront at Galion Resort in Old Town

Key West Historic District
9.6 out of 10, Exceptional, (93)
"Enjoyed our stay at Galleon"
United States
Kay c.
Luxury Waterfront at Galion Resort in Old Town

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Key West
8.8 out of 10, Excellent, (30)
"Great place, great location, great communication from host!"
United States
Lara P.
The price is HK$2,957
HK$4,434 total
includes taxes & fees
10 Dec - 11 Dec
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

2.0 star property
Old Town Key West
Treehouse Condo 2nd Floor Balcony sleeps 6 free parking

Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

Old Town Key West
9.8 out of 10, Exceptional, (33)
"Good place to stay loved it"
United States
Charles I.
The price is HK$1,152
HK$3,112 total
includes taxes & fees
10 Dec - 11 Dec
Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

Beachside
9.8 out of 10, Exceptional, (48)
"Wonderful view, lot's of space, great location "
United States
Valerie
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Lower Sugarloaf Key Hotel Reviews

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